(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-6-((S)-4-(2,4-dihydroxyphenyl)butan-2-yloxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

ID: ALA3100135

PubChem CID: 71768560

Max Phase: Preclinical

Molecular Formula: C22H34O13

Molecular Weight: 506.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](CCc1ccc(O)cc1O)O[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C22H34O13/c1-9(2-3-10-4-5-11(25)6-12(10)26)32-21-19(31)17(29)20(14(8-24)34-21)35-22-18(30)16(28)15(27)13(7-23)33-22/h4-6,9,13-31H,2-3,7-8H2,1H3/t9-,13+,14+,15+,16-,17+,18+,19+,20+,21+,22-/m0/s1

Standard InChI Key:  ZRDADUROYMLJRH-AISUOSFOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3100135

   (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(2S)-4-(2,4-dihydroxyphenyl)butan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 506.50

Molecular Weight (Monoisotopic): 506.1999

AlogP: -2.94

#Rotatable Bonds: 9

Polar Surface Area: 218.99

Molecular Species: NEUTRAL

HBA: 13

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 13

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.54

CX Basic pKa: ┄

CX LogP: -1.79

CX LogD: -1.80

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.16

Np Likeness Score: 1.75

References

1. Iwadate T, Kashiwakura Y, Masuoka N, Yamada Y, Nihei K..  (2014)  Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.,  24  (1): [PMID:24332496] [10.1016/j.bmcl.2013.11.063]

2. Iwadate T, Nihei K..  (2015)  Rhododendrol glycosides as stereospecific tyrosinase inhibitors.,  23  (20): [PMID:26386819] [10.1016/j.bmc.2015.09.014]

Source

Source(1):

• Scientific Literature